1. Field of the Invention
This invention relates to (i) 5-(4-vinyl- or 4-ethynylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and the pharmaceutically acceptable, non-toxic alkyl esters and salts thereof; (ii) the use of these compounds as anti-inflammatory agents, analgesic agents, platelet aggregation inhibitors, fibrinolytic agents and smooth muscle relaxants (this includes both prophylactic and therapeutic use); (iii) pharmaceutical compositions comprising a compound of this invention and at least one pharmaceutical excipient; and (iv) processes for preparing the compounds of this invention.
2. Related Art
Compounds are known which are represented by the formula ##STR2## wherein P is a moiety selected from the group consisting of ##STR3## in which
X is oxygen or sulfur,
R is hydrogen, methyl, chloro or bromo, the R substitution being at the 3, 4 or 5 positions of the thiophene ring,
R.sup.1 is hydrogen, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group having from 1 to 4 carbon atoms, chloro, fluoro or bromo, the R.sup.1 substitution being at the ortho, meta or para positions of the phenyl group, and
R.sup.2 is hydrogen, lower alkyl having from 1 to 4 carbon atoms, chloro, bromo, lower alkylthio, lower alkyl sulfinyl or lower alkyl sulfonyl, and R.sup.3 is hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
The compounds represented by Formula (IA) and (ID) are disclosed in U.S. Pat. No. 4,087,539, issued May 2, 1978 to Muchowski et al, while compounds of Formulas (IB) and (IC) are disclosed in U.S. Pat. No. 4,089,969, issued May 16, 1978 to Muchowski et al and U.S. Pat. No. 4,097,579 issued June 27, 1978 to Muchowski et al, respectively.
Compounds of Formula (IB) wherein R.sup.1 is methylsulfinyl or methylsulfonyl are disclosed in U.S. Pat. No. 4,232,038, issued Nov. 4, 1980. Compounds of Formula (IB) wherein R.sup.2 is chloro or bromo are disclosed in U.S. Pat. No. 4,344,943, issued Aug. 17, 1982. Compounds of Formulas IB and ID wherein R.sup.2 is lower alkylthio, lower alkylsulfinyl, or lower alkylsulfonyl, are described in copending U.S. application Ser. No. 386,174, filed June 8, 1982. All of these compounds are useful as anti-inflammatory agents, analgesic agents, platelet aggregation inhibitors, fibrinolytic agents and smooth muscle relaxants. They can be used both prophylactically and therapeutically.